


The List

by rubyrose82



Category: Once Upon a Time (TV)
Genre: F/M, Smut
Language: English
Status: In-Progress
Published: 2017-06-01
Updated: 2018-04-19
Packaged: 2018-11-07 20:02:27
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 15,704
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11066121
Author URL: https://archiveofourown.org/users/rubyrose82/pseuds/rubyrose82
Summary: When Killian comes across a list that Emma made when she was a teenager things get awkward but then soon take a sexy turn!





	1. Chapter 1

**Author's Note:**

> Sorry that it took me so long to write this! I’ve had the craziest past two weeks. I struggle with chronic pain and it’s been on bitch of a week so focusing enough to write has been a struggle. I hope to have another story or update done this week! Let me know if you want me to continue with this story. I think it could be kind of fun to write another chapter! There sure is a lot of possibilities! This idea just kind of came to me. And I mean we all have a list... No? Just me? Okay... heheheh I hope you enjoy! Oh and - means crossed off. It was the only way I could format it on this sight!

“I think this is the last of it. Is this really all you own?” Killian questioned with a rather large box in hand, kicking the door shut with his foot before swaggering back to Emma. He set it down on the dining room table amongst the other boxes while she smiled endearingly up at him from the floor where she was sorting some old childhood photos and knick knacks.

 

“Yup, this is it. Seven boxes is the rest of my life. It’s mostly clothes anyways,” The blonde explained, ripping the tape off another package. Emma had just gotten the rest of her belongings out of storage from when she lived in New York from the missing year. She had meant to do it a lot sooner, but between her family, being sheriff again, and the newest threat the Snow Queen, getting her old sweaters and silverware were the least of her worries. She thought she would have to drive back into the city to get her possessions but she was able to get her old neighbor to mail them to her instead, making her life a lot easier. Killian had generously offered to help her unpack and sort her things allowing them to spend some much needed quality time together.

 

They had been officially dating for just a few weeks and things were surprisingly going very well. He had broke down her walls and proved to her and her family that he was worthy of their trust. Even her father had taken a shine to her new boyfriend. Emma was pulled from her train of thought when her phone rang. She quickly reached for it on the kitchen table before picking it up.

 

“Sheriff Swan,” She answered officially. “Oh, that was fast. Thanks I’ll be there in two minutes,” Emma responded with a delighted smile upon her face.

 

“Who was that, love?” Killian asked as he tore open another box with his hook. He really did look for any excuse to use that thing.

 

“It was Granny. Our food is ready to be picked up. I’ll be right back,” She told slinging her purse around her shoulder before heading for the door.

 

“Are you sure you don’t want be to come with you?” He replied walking towards her.

 

“No it’s okay. I’ll just be gone a second,” Emma smiled with a sarcastic twinkle in her eye. Leaning in she placed a chaste kiss to his lips before making her way back to the door.

 

“I’ll miss you,” Killian voiced, calling to his Swan. She flashed him a saucy grin, rolling her eyes at him.

 

“I’ll miss you, too,” Emma laughed, closing the loft door with a soft thud. Once his girlfriend had left he went back to his task of opening boxes and sorting their contents. He lifted a particularly heavy one onto the table, tearing the flaps open. The package was filled with a variety of books and what appeared to be journals.

 

Killian started to unpack them one by one, admiring her taste in novels when a folded piece of paper fell out of one of the book jackets and onto the ground. At first he thought it was a page from the book, but it looked much older and wrinkled than the paperback in his hand. He bent down to retrieve it, studying it carefully while unfolding the seemingly old note. Hook examined what appeared to be a number list with some things crossed off. It read as the following:

(- means crossed off)  
1\. Skinny dipping-  
2\. Threesome-  
3\. Mirror sex  
4\. Handcuffs  
5\. Role play-  
6\. Watch porn together-  
7\. Make a sex tape  
8\. Anal  
9\. Sex on the beach-  
10\. Sex in the woods  
11\. Sex with someone older than me-  
12\. Elevator sex  
13\. Strip tease  
14\. Use a sex toy on your partner  
15\. Ride someone's face  
16\. Have sex with an uncut man  
17\. Have sex in a twin bed-  
18\. Kitchen sex  
19\. Create my own sex position-  
20\. Third base at the movies-  
21\. Masturbate together  
22\. Have sex more than 10 times in one day  
23\. Have a g spot only orgasm  
24\. Have sex in someone else's bed-  
25\. Phone sex-

There were some numbers that Killian didn't quite understand, but he could make a pretty good educated guess based on the rest of the list. He wondered when his Swan made this fantastic piece of art. He read the list over and over, attempting to make some sort of sense to it when in walked Emma. 

 

“Sorry that took a little longer than expected. I had to wait for your curly fries, they weren't quite done yet. I hope you didn't get too lonely,” She teased walking through the entryway with two togo bags in hand. Swinging back around to close the door, her long golden tresses cascading down her leather cover shoulders.

 

“Not a problem, love. By the way, what does uncut man mean?” Killian casually asked, papers still in hand. Emma looked slightly stunned and confused. He was known for his curious tendencies, always trying to learn more about her world but it was kind of a weird question even for Killian to ask out of the blue.

 

“That was random,” She laughed at him, setting the food down on the counter.

 

“Well it’s number 16. Have sex with an uncut man,” Killian read aloud, his loud booming voice echoing throughout the apartment. He watched Emma’s face go from her usual pale glow to a deep red that spread down to her neck. She instantly made the connection, running over to him as fast as she could.

 

“Oh my God, where did you get that?!” She fretted, attempting to grab the list from her boyfriend's hand. He could tell that she was completely mortified, but there was still a shimmer a humor that he could see in her eyes. Killian chuckled as he watched Emma jump to reach the paper that he was currently waving high in the air above his head. When she finally caught it, he could see relief spread across her face.

 

“Oh don’t worry, love. I have a photogenic memory. That list in all up here forever,” He teased pointing to his head. Emma let out a childish whine before hiding her face in her hands. “Spill, Emma,” Killian smiled teasing her while rubbing large circles into her back.

 

“What do you want to know?” She sighed, staring down at the page that she now definitely regretted making.

 

“Everything,” Hook laughed, encouraging her to share.

 

“Well, I made this list back when I was just barely sixteen. Back when Lily and I were best friends. We were hormonal and obviously sex crazed teenagers and we read in a magazine that every girl should make a list of their most desired sexual fantasies. So we both made one. And until now I totally forgot it even existed. There. Happy? But now I wish I never would have made that stupid list cause now you're never going to let this go for all of eternity,” Emma groaned, letting out a sarcastic cry into his chest.

 

“So you’re saying that if there crossed off it means what? You’ve done it?” Killian questioned lifting a single eyebrow to her.

 

“Yeah,” She confessed, still buried into the crook of this arm. He could tell that Emma was pretty motified by the whole ordeal but for him it was kind of exciting and arousing. Granted they had only been intimate for a week or so now, but he couldn't wait to cross off a few more items for her list. He was intrigued but also feeling fairly jealous. What other man received the pleasure of completing these activities with his Emma?

 

“You mean to tell me that Emma Swan has had a threesome?” Killian hysterically began to chuckle. So much that his abs started to hurt! “With who? Do I know him?” He questioned, on the verge of tears from laughter. Emma pressed her lips together and avoided eye contact at all cost. Crossing her arms she stared at the ceiling and sighed. Her silence gave her answer away and confirmed his suspicion. “Neal?! You had a threesome with Neal? When? And with who?” Killian’s jaw dropped to the floor.

 

“Yes with Neal it was his idea and I was young. So young, it was with some random girl that we picked up in a bar. It was his fantasy not mine. I didn't even really want to do it,” Emma reassured her boyfriend who was still smiling and laugh at her expense. “Wait so you're not mad?” She asked while her pirate still was giggling like a schoolgirl.

 

“Mad? Of course not! Emma you should never be ashamed of what you want or desire. And if I can help give you that it would be my pleasure. It would be my honor to help you cross every item off this list. In fact I think we could even extend this little list of yours. If you want of course. I think a woman who takes what she wants is incredibly sexy,” Killian admitted, slowly making his way behind her while he pressed sensual kisses to her neck. She felt his hook and hand slowly slid around her waist, pulling her in tightly against him.

 

“And you don't think these ideas are too scandalous?” She smirked, already feeling the answer to her question against the crease of her ass. The whole ordeal obviously was a huge turn on for him to respond this quickly.

 

“I’m a pirate, love. Your wildest fantasies are my Saturday night,” Killian teased while nibbling the soft skin of her ear lobe. “So what do you want to cross off first?” He wondered giving her a sexy smirk paired with an eyebrow wiggle. The question going straight to Emma’s core. Killian could feel the intense heat radiating off her body.

 

“Well, I’ve kind of wanted to tackle number 23 but no man before has been quite up to the task, but I think you may be able to,” She challenged him, flashing him a saucy smirk. Emma knew that her leggings were probably borderline soaked by now.

 

“And what's number 23, love?” Killian quipped playing with the seam of her top as his calloused hand teased her soft skin. Emma’s abs hardened when she felt his fingertips nudge further up her torso.

 

“Having a G spot only orgasm. Oh that means…” She began, thinking that there was no way her 17th century boyfriend had any idea what a G spot was. Hell, it was just recently that she figured out what it was!

 

“I know what it means love,” Killian cut her off before Emma made any botched attempt at explaining it to him.

 

“You don’t know what uncut means but you know what the G spot is?” Emma lifted an eyebrow giggling in disbelief. A smile plastered on both of their faces as he buried his nose in the crook of her neck, inhaling the sweet subtle scent of her perfume.

 

“Priorities, love. And not only do I know what it is, but more importantly I know where it is…” And with that Emma felt a bolt of pleasure shoot right to her clit. Even though she was a grown and very sexually mature woman, Emma was always a one night stand kind of girl. Which usually never resulted in much satisfaction on her end. It was just enough to scratch an itch. Nothing less and nothing more.

 

The longer relationships that she did have with Neal and Walsh never really yielded much enjoyment. Neither one of them really clicked with her sexually. There always seemed to be a lot of fumbling and Emma learned that it was easier to fake an orgsam then to lay there for hours while watching them try. But Killian in their short time being intimate had gotten her close a number of time. He always put her pleasure over his, making sure that she came one way or another, but Emma wanted to know what it felt like to be pushed off the edge without touching her clit. It was a completely foreign concept to her. She couldn't even do it herself. At one point she even thought there may be something wrong with her until she read in a magazine that it wasn't all that uncommon. That’s what landed it on her list to begin with. There were a lot of adventurous things on Emma’s list but this wasn't really one of them. And she hoped that Killian was able to deliver.

 

Without any warning Killian spun Emma around and his lips were on hers in a second. Tugging on her bottom lip, Killian demanded entrance which Emma was happy to give. Her body felt like it was on fire. Every molecule of her being was on edge and completely aroused. She felt his hard aching member press against her stomach. A wonderful reminder of that satisfying stretch that ripples through her whenever he's inside her. Soon Emma’s red leather jacket and white tank top were thrown to the ground and all she was left in was her lace bra and jeans. His thumb hooked itself around one of her straps, easing it down her shoulders. He softly brushed the pad of her fingers over her hardening nipple, creating puckered peaks through the fabric. She wanted desperately to tell him to get on with it and end this torture for both their sakes, but Emma was unable to form a coherent sentence. Killian was still mostly dressed, too clothed for her liking. But before she could move to remove any of his garments, Emma was being lifted onto the kitchen counter, knocking random utensils that were previously lying on there. This position allowed them both to be more face to face, almost feeling a higher level of closeness or intimacy.

 

He kissed his way down her neck, stopping just below her collarbone. It was a place that Killian knew made her fall to pieces in just the short time they were together. Emma groaned as she felt his hand and hook make its way behind her back. She knew his intentions when he started to fumble around trying to unhook her bra. Wanting to speed up the process, she too reached behind herself, aiding with the garment before tossing it to the floor with the rest of her clothes. A rush a nervousness flooded through her. What if she can’t come? She’s never done it before. At least not like this. Not even when she tries it herself. Is it her? Is there something wrong with her? If he doesn't succeed will it be awkward between them? After all they hadn't been together for very long.

 

“Emma, darling, I can hear you thinking. There are no villains, no nagging parents, and no responsibilities here. It’s just you and me,” Killian smiled, staring into his Swans eyes.

 

“Sorry,” Emma mumbled, leaning her forehand against his.

 

“Don’t apologize, love. Just let me make you feel good,” He vowed as she hooked her legs back around his trim waist. Emma felt herself being lifted once again while getting lost in yet another soul shatter kiss. Hook carried her across the apartment and up the stairs to her room.

 

Playfully, he threw her on the bed with a light bounce. She let out a carefree giggle which seemed so out of character for her. Emma watched him slowly remove his newly bought wardrobe piece by piece. She had the perfect view to admire how every muscle in his body rippled as he took off each article. God, she would pay money to just watch this man undress. Soon all he was left in were his boxer briefs that he still wasn't quite used to wearing yet. Emma was still breathing pretty hard, her cheeks all the way down to her breasts were flushed a light tinted red from her arousal. Her golden curls cascaded down the tops of her shoulders.

 

Killian leaned down, slanting his lips over hers once again. She let the sensation take her, already feeling an ocean between her legs. Emma dragged him closer, pulling him on top of her, running her fingers through his dark locks, both dueling one another for dominance. Hook kissed down her neck all the way to her perfect breasts. He took his time sucking, biting, and licking each one. Paying extra attention to her pink nipples. Blowing cool air on each of them until they were hard over sensitive points and Emma was gasping for air. Killian made his way down further until he reached the seam of her jeans. Carefully he single handedly popped the button to her pants, pulling them down with his hand and hook until only a thin blue strip of fabric covered her center.

 

“I’ll never grow tired your silky skin, or your gorgeous legs, or the way you smile with your eyes when you walk into a room,” Killian growled, ghosting down her body. “You Emma Swan are what men refer to as timeless,” He moaned from between her legs.

 

“You don't have to flatter me you already got in my pants,” She smiled, biting her bottom lip while glancing down admiring her lover’s ministrations. Hook continued to nibble the insides of her thighs, working her up, pushing her higher and higher until she felt as if she might implode from all the built up sexual tension.

 

“I want you to tell me everything you feel. Don’t be afraid to tell me what you like and what you don’t,” He ordered while pulling her lace panties down using his hand and teeth. Killian could already see her arousal glistening down her folds. A soft moan slipped out of her lips as Emma felt his teeth graze her perked nipples. He took a supple breast into his mouth, sucking it lightly while he used his hand to massage its twin. Her hands instantly flew to his hair once again. Emma’s back arched attempting to get as close as she could to Killian wicked mouth. Suddenly his lips were being pulled back to hers. It was a messy and needy kiss, but neither of them could bring themselves to care. Emma could feel his clothed member that was still confined in his boxers against her stomach, which only increased the burn and desire for him. She was desperate to feel him inside her but she could tell that she was gonna have to wait a while for that.

 

Killian made his way back down her body, stopping briefly to pay extra attention to each breast before stopping between her legs once again. He slid a single finger through her slick folds, parting them slightly. Slowly and with great care he then inserted one digit into her aching center. Emma whimpered at the intrusion. Gradually Killian massaged her inner walls, experimenting and listening intently to what felt good. It didn't take long for him to soon figure out exactly what she liked. Hook added another finger into her slippery sex adding more constant yet satisfying pressure.

 

“Fuck,” Emma whined, loving the stretch of the second digit. At a leisurely pass Killian continued to pump in and out of his Swan while he kissed the insides of her arousal coated thighs. The heavy breathing and high pitched moans were music to this pirates ears. Emma was worked up almost to her breaking point. Everything that Killian was doing was magic, but it wasn't quite enough. She felt as if a any second she could fall off the edge, but something was holding her back. Emma was teetering, so close to finally letting go when Killian pushed his two fingers up quickly over and over again. It was almost as if he was tapping the tops of her walls, massaging the aroused muscles. After mere moments Emma fell off the cliff. An intense wave of pleasure continued to wash over her, shaking her entire body. She had never felt anything quite like it before. Her whole body felt as if she was flying. Emma’s breathing was still erratic and she could almost swear she could hear her own heart beating.

 

“Get inside me right now, pirate,” She growled, dragging him up from between her legs. She ripped off the last piece of fabric that separated them and in the matter of seconds Killian was sliding into her aching center with ease. She reveled in the satisfying stretch that only he could provide. His fingers were heaven, but his cock was paradise. After only mere moments of mingled moans and the squeaking of the floor boards, Killian lifted her up slightly encouraging her legs to lean flat against his chest and her feet propped over his shoulders.

 

The position change deepened the angle, intensifying both their pleasure. It was a sensation Emma had never quite felt before and she was so glad that it was Killian that was the first to give it to her. Hook could feel that she was close. Every thrust created a rippled effect. Her inner walls fluttered around his member, testing his stamina. He so desperately wanted her to fall one more time before joining her on the other side. Killian increased his speed, pounding into her at a punishing pace.

 

Emma fisted the sheets in her hands as she came once again. Her eyes flew shut. She could have swore she saw a bright white light followed by stars that flashed before her eyes. Her walls clamped down on him as she came, pulling him down with her. Killian came with a shout, filling her up with his seed. They both slowly came down from their highs as Killian fell down next to his Swan, doing his best not to crush her.

 

“You found it,” She smiled staring up at the ceiling, the euphoria still coursing through her veins.

 

“Did you ever doubt I would. After all, I am a pirate. Finding buried treasure is kind of what I do,” He chuckled into the crook of her neck, kissing the skin still exposed. “And hey you never told me what uncut means,” He wondered as Emma snuggled in close between the sheets. She instantly giggled remembering their previous conversation.

 

“It’s another word for uncircumcised, or in other words what you are,” She explained pointing downward. It took him a moment to make the connection but finally Emma saw everything click in his expression. Killian reached over to her night side table picking up her list along with a pen in her draw. She watched him cross off two items with a smile.

 

“I’d say it was a pretty successful night. We killed two birds with one stone,” Hook noted while continuing to admire the rest of the unchecked items.

 

“I would have to agree. I even think you earned the right to pick the next number off the list,” She suggested, giving him the bedroom eyes once again.

 

“I would be beyond honored,” Killian grinned, looking as if he just won the lottery. Emma would never say this out loud or even admit it to herself but what she felt in this moment was love. It was a feeling in her heart that she hadn't felt in nearly a decade but she wanted to hold on to it as long as she could.

 

“What about you? Do you have a list?” Emma flirted wanting to lighten the mood as she played with the coarse hair on his chest.

 

“Wouldn't you like to know,” Killian replied.

 

“Maybe I would.”


	2. Chapter 2

**Notes for the Chapter:**

> Here is Chapter two of The List! Sorry it took a day more than I expected but I hope it was well worth the wait! Even though this is chapter two you don't have to necessarily read the first one for it to make sense. Of course I encourage you to read in any way! I can’t wait for chapter three! What do you think these two crazy kids should do next? And what do you think Killian has on his list? *Disclaimer* This is a little more scandalous than what I usually write. It definitely isn't strictly vanilla but it really isn't that risque, but I just thought I should warn you! If smut isn't your thing than don’t read! I hope you enjoy!

“So let me get this straight. It’s your birthday but you're giving me a present?” Emma grinned lifting an eyebrow gazing upon the gift currently sitting on her dining room table. The bag was surprisingly aesthetically appealing, jazzed with red ribbons and white tissue paper that was lightly flecked with sparkles. When did her pirate learn gift edicate? 

Today was her boyfriend's birthday and they had plans to go on a romantic dinner date with good food and the soft glow of candlelight. Emma was already dressed in a sleek sexy black dress that hugged each curve perfectly accentuating her breasts and waist. The sight alone was enough of a gift for Hook.

“Oh trust me, love. This is my present,” Killian flirted, lifting the bag up by his hook handing it to her. 

“Okay weirdo,” Emma remarked taking it from her boyfriend. She began to slowly pull the paper from the bag setting the wrapping on the table behind her. Once she removed the packaging Emma pulled out a pair of red lace underwear. A thong to be exact. It definitely wasn't what she was expecting that’s for sure but Hook had good taste at least when it came to things like this. 

“You got me panties?” Emma laughed looking puzzlingly into his gorgeous blue eyes searching for an explanation. Killian flashed one of his famous cheeky grins before stepping in closer. 

“Oh, love, these arent just your everyday old panties. What you hold in your hand is man’s greatest invention,” Hook told seeming almost borderline insulted at Emma’s tone. 

“I thought you told me nutella was man's greatest invention,” She teased giving him a playful chuckle. 

“See this even beats nutella,” He grinned darting out his tongue to wet his lips. Damn the man was sexy. He had awoken something powerful deep inside her. He was like a drug that she couldn't get enough of. 

“Okay, I’ll bite. What's so special about these?” Emma implored while inspecting the fabric. 

“It’s easier if I show you. Will you try them on for me?” His chin pointed down and his eyes gazing up, flashing her the puppy dog look. She simply smiled with the panties in hand, quickly turning around with a little extra pep in her step and more swing in her hips. He watched her disappear up the stairs to change. It only took her mere moments to put them on. 

“Okay, now what? Are you gonna rip them off me like you do to every other pair that I own?” Emma snarked skipping down to the base of the stairs. That’s when all of a sudden she felt an incredibly unexpected jolt of pleasure vibrating throughout her body. The sensation started between her legs but grew, making her legs go weak. And then as quickly as it came, it stopped. Emma was a little taken aback. The pleasure had fogged all objective thinking and she had no idea where it came from until she saw Killian pull a small shiny black remote from his leather jacket pocket wearing a devious grin. 

“Was that what I think it is?” Emma asked still trying to catch her breath from the rush of desire coursing through her veins. 

“I recently payed a visit to a shop for adults and it caught my eye,” Killian growled wiggling his brows like the sex god she knew he was. 

“Vibrating panties...I don't remember these being on my list, pirate,” Emma grinned giving him her famous side eye while making her way off the rest of the stairs walking towards her newly modern dressed boyfriend. 

“That’s because they aren't on your list. They’re on mine,” Hook winked, moving in closer wrapping his hand and hook around her curves. “

“You’re trying telI me my two hundred year old boyfriend put vibrating panties on his list? Besides I thought you said you didn't have one,” She quipped flashing him a questioning glare. 

“I didn't, but know I do. You could say someone inspired me. And you did say I get to pick the next item. That is of course if you are open to the idea,” Killian chuckled with a borderline beg in his eyes. Emma could tell the idea excited him to say the least. She could already feel his hardening member begin to twitch against her stomach. And she had to admit the fantasy had popped into her mind a time or two. The thought of him having full control over her pleasure like that had blood rushing between her legs. She leaned in to give him a peck on the lips agreeing to his fantasy. But what was supposed to be a quick kiss rapidly turned into a full blown makeout. 

“Easy tiger, our dinner reservation is in twenty minutes. Let me just take these things off and I’m ready to go,” Emma chimed in placing one last kiss to Hook’s swollen lips. But before she turned around the make her way up the stairs Killian had that look in his eyes. The look he would always get right before he would beg her to do something that she usually did not want to do. 

“What?” She implored with one hand on her hip shifting her weight to just one of her kitten heels. And then everything clicked. She knew exactly what her pirate wanted. It was what every man wanted. A chance for complete control over her pleasure even if it was just once. 

“No,” Emma sternly replied pointing firmly in his direction.

“How do you even know what I’m going to say?” Killian asked with a pleading tone as he inched closer to her.

“Because Killian Jones you are somewhat of an open book, love,” She mocked flashing him a cute smile.

“Please? I promise you that you will enjoy it. And when we get home your wish is my command. Whatever your heart desires, consider it done,” Killian assured while his hand wandered down over her ass giving it a light squeeze.

“Anything?” Emma confirmed with a little twinkle in her eye as she smoothed her palm over the hard planes of his chest. The thing was, Emma actually was very open to the idea. The thought of him pleasuring her in public like that in front of half of Storybrooke had her getting hot and bothered, but he didn’t have to know that. And there was one thing on her list that she knew she would have trouble getting him to try. It was really a win win for both of them.

“Well then, let's go. I would hate to be late,” Emma strutted to the door, Killian following closely behind her like a dog following his master. They set up a few ground rules on the car ride over. They even formed a safe word “ocean” that Emma could say that would seize everything immediately even though she had no intention of stopping this train. 

A mixed rush of pleasure and adrenaline flooded her body as the sensation of came her in the passenger seat. Once they were parked downtown Emma knew her panties were nearly soaked through but she couldn’t find the energy to care.

Killian and Emma walked arm and arm into Storybrooke’s newest restaurant. He decided to give Emma a little break from his ministrations as they strolled to their reserved table for two. They were lost in conversation, sharing, and laughing. Emma almost forgot about the dirty little secret under her dress. Killian picked out an appetizer off the extensive menu and ordered Emma a glass of red wine. 

“Have you decided what you would like tonight, or do you need a few more minutes?” A young waitress ask smiling at the both of them. Her dark high ponytail shined in the soft glow of the candle light as she clicked her pen, ready to take their order. Hook always got the same thing at every restaurant. White fish, lightly fried with broccoli and mash potatoes. Emma thought that after centuries of eating seafood, he would grow rather sick of the stuff by now. But not Killian. He would eat anything that came out of the sea morning, noon, and night. Emma on the other hand was far more adventurous. She tried something new each place she went. 

She was stuck between two items when that final buzz radiated throughout her body accompanied by Hook’s signature smirk and smolder. She arched her back in her chair, the pulsation rhythm changed completely, catching her slightly off balance. Emma could have swore the whole restaurant could hear the vibration of her little secret tucked into her panties. All thoughts flew from her mind once she felt that wondrous pleasure coursing through her veins. Killian loved watching his Emma teetering on the edge in public at his hand. She gripped the side of the table, trying anything to ground herself. She tried to focus on anything else other than the pleasure under her dress that she ended up reading the same sentence fifteen times.

“Are you alright, love? You look a bit flush?” Killian mocked with a pleasing grin.

“I can come back if you need another minute,” The brunette waitress replied looking slightly confused and uncomfortable at Emma’s strange face and mood swings. She was almost came right there and then until as suddenly as it appeared, vibration stopped.

“Excuse me ma'am. Would you like me to come back?” She tried again placing her hand on her hip.

“Oh sorry, I’ll have the mushroom ravioli with a side salad no tomatoes,” Emma muttered still holding on to the table for dear life. Hook simply took a sip from his rum attempting to hold back a chuckle until the server left.

“Not fair,” She sighed with an annoyed glare.

“What’s that, love? Having second thoughts on your order tonight?” Killian mocked.

“It’s incredibly cruel to withhold an orgasm from a woman,” Emma whispered across the candle lit table.

“Oh but I can. I read it in a magazine this week. I think it’s called edging? I saw it in the waiting room when you made me go to that horrid place where they poked around in my mouth with all those sharp medical instruments. But the article was quite educational. Apparently this technique makes the ending that much sweeter,” Killian whispered across the soft glow of the candle light as he wiggled his brows. She had to admit, seeing her man with complete control this this was a huge turn on. She had no idea this was such a fantasy of hers. Emma’s chest was still heaving and a faint sheen of sweat shined between her breasts. She reached for her glass of wine, knowing she was gonna need it to get through the rest of the night. 

By the time dessert rolled around they were playing footsie under the table and sucking whip cream off their fingers. The rush of dopamine made the food taste so much better. It was like a completely different experience. During the dinner Emma had only come once over the course of almost two hours. She thought she was at the peak of her arousal. The whole ordeal was obviously turning Killian on as well. The evidence was pressing against the zipper of his jeans. The sexual tension on the car ride home was so thick they could both barely breathe. They made their way back to her apartment walking hand in hand up the stairs.

“You wanna come inside for some coffee?” Emma teased, recalling their first date. She wrapped her arms around his neck, pulling him in for an earth shattering kiss. Biting and tugging one another's lips, dueling for dominance as they both got lost in the throws of passion. Even when she pulled away he could swear he could still feel her lips on his.

“Bloody hell, Swan. That felt like a request,” Killian muttered resting his forehead against hers while his hook and hand wandered down to her tight ass. Emma dragged them both into the loft with a love struck smile upon her face.

“Because it was,” She giggled, kissing his neck as she ran her fingers through his hair. “Now earlier before dinner you said that we could do anything I wanted. Is that still true?” Emma flirted, whispering in his ear.

“Yes, love I do believe that is what I said,” Hook flashed her a devilish grin, playing with the seam of her skin tight dress, pulling it up to expose the soft skin of her legs. 

“Anything?” Emma confirmed running her fingers through the coarse dark hair on his chest.

“How many times are you gonna ask me that, Swan? Your wish is my command,” Killian promised, nibbling on her ear lobe.

“Then I’d like to show you something,” She smirked, dragging her hand down to interlock her finger with his. Emma led him up the stairs to her room with Hook following with a smile upon his face close behind. “Did you see any other toys at the shop?”

“I did some browsing, why?” Hook questioned, wondering where this was going.

“I just had a few ideas I wanted to try out. Another item I want to cross off my list. If that’s okay with you,” Emma smiled.

“Are you gonna ask me to close my eyes?” Killian jested, giggling behind her, burying his face in the crook of her neck as the both paused at the top of the stairs.

“Actually that’s a pretty good idea,” Emma flirted batting her eyes at him. “Take off your clothes and lie down, birthday boy. It’s time for your real present,” She requested pushing him back onto the bed with a slight bounce. Killian didn't have to be told twice. He quickly discarded his garb, awaiting his Swan’s next instruction. 

Emma sauntered over to her nightstand and opened the top drawer. She carefully removed a wooden box that was shoved all the way back covered behind clutter, many books and knickknacks. The mystery intrigued Hook as he watched her open the top. She carefully removed a small silver cylinder that resembled a bullet and a pink over sized phallic shaped object that he guessed was supposed to look like a penis that was honestly incredibly intimidating to say the least. And lastly she took out a bottle of clear liquid. He remembered seeing some of these items in the shop that he visited just the day before, but he thought that these were for women not men. He knew that this was number #14 on Emma’s list but he didn't think they would jump into it as their second item that they would cross off. But Killian decided that he was gonna trust Emma and go along with whatever she had in store.

“I only have three rules. No touching me or yourself and I want to hear everything you're feeling. Got it, pirate?” She commanded.

“Yes ma’am,” He mocked. Her demanding demeanor was obviously turning him on by the looks of his cock twitching against his rock hard abs. The sight gave Emma an extra boost confidence. Knowing that she could excite her man just purely by talking to him shot hot waves of pleasure between her legs.

Emma walked to the end of the bed where she knew he had a full view of her toned body before she began to shimmy off her skin tight dress. His eyes grew wide and dark with lust at the sight. Soon all she was left in were her see through black bra and red panty set matched her pair of sexy garners. Hook’s mouth went dry, and for the first time in their whole relationship he was completely speechless. 

“What? No famous Captain Hook innuendo? No sexy eyebrow dance? What did you do with my boyfriend?” Emma teased, sauntering over to him.

“Bloody hell, woman. You’re gonna kill me,” He chuckled, dropping his head back down to the bed. She strutted over to the right of the bed, gracefully moving to the pillow that was under Killian’s head. She straddled it now inches away from him, her thighs perfectly framed his head and her golden tresses cascaded down her shoulders. Her center was so close to him he could smell her arousal centimeters away driving him completely mad. Leaning down she took an earlobe between her teeth, playing with his earing. Emma moved to his neck, sucking on the delicate flesh accompanied with the slight scratch of his ginger flecked scruff. By the time she made it to his lips Killian was practically begging to kiss her again. Their soft lips mingled and their tongues dueled passionately as they gasped for air. Emma’s perky breasts were hovering just over his eyes as she traveled further down his well toned body. Killian’s hook and hand automatically raised up attempting to hold on to anything. He tangled his fingers in her hair gathering it to one side of her shoulder. 

“No touching, Jones,” Emma growled, covering his body with love bites. She circled his nipple with her tongue until the sensitive flesh was a puckered peak. Emma then bit down hard enough to hear his breath hitch. The intense sensation of pain and pleasure raced through his veins. At this moment she felt something she had never felt before. She was loved, wanted, sexy, and in control. It was a feeling she could get used to. Hook always made her feel wanted and loved but this was a new level that she wanted to explore to its fullest. 

“Just relax, love,” Emma mocked reaching for the a bottle of sweet smelling oil. She poured a generous dollop into her hands, rubbing them together before smoothing the massage oil all over his body. She first started with his pecks, lathering his gorgeous chest easing his muscles into a state of an odd mixture of arousal and relaxation. Emma listened to him take deep calming breathes. She then swung her feet to the side of the bed grounding them to the floor once again. With a sway of her hips she strolled back to her little wooden box on her night stand. 

“Do you trust me?” Emma smiled with one hand on her hip.

“Always,” Killian promised, his member beginning to twitch as his imagination ran wild with thoughts of what he knew was yet to come.

“Good,” She grinned so wide her nose wrinkled a little as she took out that little little silver bullet looking thing he remembered seeing just a few moments back. The object had a long wire that connected to a black remote with a few buttons and a single dial. Emma pressed one of them and a soft buzz filled the air. It reminded him of him of the sound his talking device would make when Emma would call him. 

“Close your eyes,” She requested from the foot of the bed. Hook hesitantly obeyed, shutting his eyes tight trusting in his Swan. He jumped slightly when the toy first came in contact with his skin. The sensation was odd yet pleasurable. It was nothing like he had ever felt before. After all, this particular item wasn't native to the Enchanted Forest.

Emma started with his nipples. Circling and playing with them until they were hard pebbles. His muscles rippled as she dragged the toy further down his torso. Expertly avoiding his aching member that was currently bobbing against his abs. With every pass of her hand his erection twitched and grew a little harder. Emma could tell he was struggling to keep his eyes closed any longer, so she thought she would end his misery, for now.

“You can open your eyes now,” She commanded reaching behind herself in order to unclasp her lacey bra. Emma let it fall from her shoulders before tossing it to the ground. She then grabbed the bottle of sweet smelling oil once more. She dropped the toy to the bed and poured some in her hand. But instead of rubbing it on Hook she lathered it all over her perfect breasts, giving them an irresistible sheen that Killian couldn't take his eyes off. Emma massaged the mounds, putting on a show she knew he wouldn't forget. She started by tugging at the sensitive skin of her rosy nipples, pulling the buds into peaks. Then weighing them both in her hands before giving them a firm squeeze. She dropped her hands down to his thighs smoothing the leftover oil up and down his toned legs. Each pass her fingers came closer to his cock but she never gave him what he truly desired. His breathing hitched once he felt her lips graze the insides of his thighs. She continued her journey up his body. Her breasts teased his member slightly when she kissed, licked, and nipped his gorgeous chest. Killian let out an audible sigh the second he felt her lips back on his. He wasted no time deepening the kiss. Emma pulled back letting out a laugh.

“Ah ah ah not so fast. Someone's impatient. After all, there’s no need to rush,” She giggled enjoying torturing her pirate just as he had the whole night at dinner. Killian playfully slapped her lace covered ass in retaliation. 

“You know the rules, Jones. Don’t make me cuff you,” Emma teased, sucking on the sensitive spot just below his ear.

“Wouldn't be the first time and I doubt it would be the last,” Hook smirked digging his hook into the bed sheets. She kissed back down his body, completely ignoring his now rock hard cock that was bobbing just inches away from her face. Straddling him just below the knees Emma picked up the toy once again, turning it back on running it in the insides of his thighs until he was a quivering mess once again.

“I always knew you’d be the death of me woman,” He moaned, letting the vibration take him as precum beaded down his engorged tip. Emma swiped her blonde curls to the side, never breaking eye contact. She started dangerously slow, dragging the bullet down his shaft, enjoying the sight of him jumping from the pleasurable vibrations at every flick of her wrist. She wrapped her lips around him, following closely behind her new partner in crime.

“What the bloody hell is that thing and why are we just using it now?!” Hook moaned as Emma took more of him into her mouth. In all of Killian’s hundreds of years he had never felt anything so spectacular. All he knew was he didn't want it to stop. She hummed in approval, loving the taste of him. Her jaw ached slightly, his size requiring her to open wider than normal to accommodate his massive cock. Emma moved the toy further south down his shaft stopping at his balls, teasing them one by one as she continued her menstruation. This combination was magic. It nearly had her pirate convulsions. He was approaching his climax embarrassingly quickly. It sensation was so powerful he felt as if he had no control over his body. But just as he was about to come Emma halted all movement, releasing his dick from between her lips and pulling the bullet away. 

“Fuck,” Killian swore, his heart was beating so fast he thought it was gonna burst out of his chest!

“I told you I’d get you back. Payback’s a bitch huh?” Emma smirked, referring to Killian’s “edging” at dinner just a few hours ago.

“I think you’ve made your point Swan,” Hook voiced as she lightly stroked his penis once again.

“I don’t know I feel like I should keep this going for at least an hour or so,” She teased flashing him a daring grin that made his heart skip a beat. 

“Please,” Killian urged, ballig the sheets in his fist.

“Well, I do like it when you beg,” Emma giggled returning to her previous ministrations. This time she didn't hold back, giving him everything she had. He had been so close he was practically teetering on the edge that it didn't take him long to climax. That’s when Emma had an idea, something she had yet to try with any partner. She moved the toy just slightly down under his balls and switched the vibrator on high, stimulating his prostate.

With a guttural cry, he stilled, pouring himself down her throat as she drank him deep, sucking every last salty-sweet drop from him. It was the most powerful earth shattering orgasm Killian had ever experienced. It was as if his whole body was soaring through the clouds. He could feel himself sink into the sheets as she cleaned him off, laving her tongue over his cock and drawing out his orgasm as he came down. 

“Get over here,” Hook growled, tearing her panties off her and dragging her core up to him as Emma let out a cute giggle. He wasted no time going to work. He was like a man dying of thirst and her pussy was an oasis. She gasped and moaned his name as he took her clit in his mouth and began to suck. He drank in the sweet nectar between her legs as she whimpered above him, grasping the bed frame for dear life. Killian secured his arm and hook around her legs, pressing her tightly to him. He drew in her hard nub, sucking her cunt greedily into his mouth until she was coming and screaming out in blissful pleasure that left her muscles convulsing and her body boneless. She collapsed to his side as they both enjoyed their euphoric highs.

“That. was. amazing,” Emma muttered, smiling into his chest. “And you ripped my panties!” She giggled.

“Oh, love I will buy you a new pair I promise you,” Killian chuckled, wrapping his arms around his Swan. “Where did you even get that little piece of paradise? I don’t remember seeing anything like it at the shop,” Hook questioned.

“Well, it’s originally just for woman to use on themselves but I wanted to try using it a little differently tonight,” Emma whispered. “Did you like it?” She wondered with a fleck of worry in her eyes.

Like it? Are you kidding me? That was the most fun I’ve ever had. I definitely want to recreate this night over and over and over again,” Killian nuzzled into the crook of her neck letting the scruff of her beard tickled her skin. 

“Well, I’m glad you liked it so much. As long as I’m not replaced by my vibrators,” Emma teased, running her fingers through his chest hair.

“Oh, love that would never happen. You’re irreplaceable. But next time I would like to see you use this toy of yours in a more traditional sense. I’d love to watch,” He insisted.

“I think we can make that happen,” Emma teased, kissing the soft skin on his neck. 

“I’d say this was a pretty successful night. We crossed two off your list and one off mine. We are very resourceful,” Hook replied.

“Speaking of your list, when I’m I gonna get to see this masterpiece you keep referring to?” Emma wondered. “Please? I showed you mine now show me yours, KIllian Jones,” She begged flashing him her famous smile that he couldn't ignore.

“I’ll show you when I finish writing it,” Hook promised, placing a kiss to her forehead. 

“Alright, deal… Emma sighed. “So did you enjoy your birthday, pirate?” She asked, smiling so bright her nose wrinkled a little.

“Everyday I spend with you, Swan is better than the last. Thank you for making today special. As you can imagine birthdays for me have always been a hard to celebrate. Especially after my brother died, but with you it’s like I can finally be happy again and not be that hateful man I once was. Thank you for that, Emma. You’re the best present any man could ask for,” He confessed. His little speech pulled at her heartstrings. She knew holidays and special occasions were hard for Killian but she never really made the connection why. She leaned in, placing a chaste kiss to his lips.

“You’re welcome. And speaking of gifts, I forgot to give something to you!” She reached over to her nightstand and pulled out a small box and handed it to him.

“Emma, you didn't have to get me anything,” Killian protested as Emma placed the box in his hand. 

“Oh shut up and open it,” She snapped, rolling her eyes. He abided her request and opened it. Inside was a small silver ring with an engraved compass shining on the top. “I know what your rings represent for you. I understand why you wear them, but I wanted you to have something that you could look at everyday to remind you of how far you’ve come. This is how we met, and I don’t want you to forget who you are now. Who I know you are now,” Emma voiced as Killian big blue eyes stared into hers. For the first time in a long time, Killian Jones was speechless. 

“I don’t know what I did to deserve you, Emma Swan,” Hook choked out, tears almost in his eyes. 

“Happy birthday, Killian.”

 

For reference this is what the list looks like now: (- means crossed off)  
1\. Skinny dipping -  
2\. Threesome -  
3\. Mirror sex  
4\. Handcuffs  
5\. Role play -  
6\. Watch porn together-  
7\. Make a sex tape  
8\. Anal  
9\. Sex on the beach -  
10\. Sex in the woods  
11\. Sex with someone older than me -  
12\. Elevator sex  
13\. Strip tease  
14\. Use a sex toy on your partner -  
15\. Ride someone's face -  
16\. Have sex with an uncut man-  
17\. Have sex in a twin bed -  
18\. Kitchen sex  
19\. Create my own sex position -  
20\. Third base at the movies -  
21\. Masturbate together  
22\. Have sex more than 10 times in one day  
23\. Have a g spot only orgasm  
24\. Have sex in someone else's bed -  
25\. Phone sex-

**Notes for the Chapter:**

> Please let me know if you would liked to be tagged in the future! Thank you so much for reading! Hope it was worth the wait!
> 
> As always please leave a like, comment, suggestion, or prompt! You can follow me @rubyrose82 or my Captain Swan Blog @captain-swan-coffee


	3. Motion of the Ocean

**Summary for the Chapter:**

> When Killian comes across a list that Emma made when she was a teenager things get awkward but then soon take a sexy turn! This chapter Emma finds his list and surprises him a task that no man has done before!

**Notes for the Chapter:**

> I know that last chapter took place on Killian’s birthday but can we just ignore that since technically the chapters can be read as one shots! Just do what we do when we watch OUAT and ignore the huge plot holes! hehehe! This chapter is definitely one of the more risque things I’ve written so this is your warning! But as always there is plot and plenty of fluff! Enjoy!

Emma glided down the sidewalks headed for Granny’s, so excited that she was able to get off work early to surprise her pirate with a gift she and her dad had been working on for months! And it was finally done and ready for the big reveal. It seemed crazy to her that Killian was still staying at the Inn after living in Storybrooke for almost five months! But the housing market in Storybrooke was no joke. Too many fairytale characters and curses and not enough houses created a hectic real estate market for the area. So Killian was stuck at Granny’s for now. 

Emma was all dressed up for her big date with her pirate. Well, more dressed up than usual at least for her. She had on a simple yet elegant dark purple silk dress. She walked up to his hotel door, fixing her hair before knocking.

Killian opened the door with his famous cheeky grin and brow wiggle. “Happy Birthday,” Emma smiled playing with the seam of her dress. “What number is this? 233?” Emma teased letting out a chuckle. 

“Ha Ha very funny… Technically it’s closer to 246 but who's counting,” Hook jested his elbow resting on the door frame. “So, what was this surprise you were talking about on the phone?” He wondered.

“If it’s a surprise then I can’t tell you,” Emma replied biting her bottom lip as she reached her hand out for him. He grabbed it, intertwining their fingers together as they walked down the hall. 

“Is it a flying monkey?!” Hook jested as they strolled arm and arm. Emma leaned in resting her head on his shoulder slightly.

“No, will you just have to wait! You’re worse than Henry when he was 10!” Emma rolled her eyes giggling her hand still in his.

“Is it a Ferris wheel?!” He grinned. Okay, now he was just doing this to annoy her.

“Will you just be patient! We are almost there,” Emma replied, giggling as they made their way to the docks.

Emma lead her pirate to the marina, watching the waves roll to the shore. The summer breeze blew through their hair as they smelled the sea air. Emma instructed Killian to close his eyes as they approached his surprise. 

This was the moment of truth. Countless hours went into this and she hoped with all her heart that it was worth it!

“Okay, you can open them,” Emma smiled anticipating his reaction, hoping he would be pleased. There before them was a modest sail boat with wood accents fit with a table and chairs in the center.

“Dinner for two, love this is the perfect birthday present,” He grinned giving her a peck on the lips. 

“Actually the dinner wasn't really the surprise,” She bit her lip, her brows elevated as she could see the wheels turning in her pirates' eyes. He went from puzzled to disbelief all in about five seconds as he read the name of the vessel on the back. It read “The Golden Compass”

“Surprise!” Emma half-heartedly threw her hands up preparing for the worst. 

Killian was speechless. After a few moments without a word from either of them, Emma finally caved. “Oh shit, you hate it don't you? I know it’s not the Jolly but I just wanted you to have a place to-” She was abruptly cut off by the loving lips of her one-handed boyfriend. He threaded his fingers through her hair lost in the happiness of their kiss.

“I love it,” Killian proclaimed running his thumb against the apple of her cheek, his piercing blue eyes staring into hers.

“You do?” Emma smiled her eyes peering up from the dock below as her shoulders relaxed, finally feeling like she could breathe again. 

“Emma, how could I not love something like this?” Hook grinned tucking a stray lock of her golden hair behind her ear. “But, how Emma? Didn't this cost you a fortune?” Killian pondered.

“Actually no, being the sheriff does have its benefits. It was repossessed and I got it for next to nothing. And for the last several weeks David, Henry and I have been restoring it,”

“But why go to all that trouble for me?” Hook pondered.

“Can’t a girl just do something nice for her super hot, adorable pirate boyfriend?” She replied wrapping her arms around his neck.

“I suppose so but this is a lot, love,” Killian protested as he moved in closer.

“Well, you gave up the thing you loved the most in the world for me. I guess I just wanted to return to you to you even a little of what you lost,” She admitted.

“Emma, I didn't lose anything. I would give up the Jolly hundreds of times if I could see you even one last time. Hell, I would burn the ol’girl down myself if it meant I could be with you. I don’t regret it at all. Not for a second,” He promised. And Emma could tell that he truly meant every word.

She gave him a quick tour of his new home. On top, the deck was a small table and a couch fit to weather any storm. Emma leads him down underneath to show him the cabin. It was surprisingly bigger than he thought it would be. Really it wasn't much smaller than his cabin on the jolly. But this room was much more practical than his old room. The bed was bigger at least a full he guessed and the ceiling height was about the length of him. The walls seemed to be made of shiplap painted white and on the opposite wall of the bed, there was a small kitchenette. It was everything he needed and it was decorated just to his liking. The quilt on the bed was navy blue and the clock above the sink was shaped like the wheel of a ship. He couldn't stop smiling. He truly didn't know what he did to deserve a woman like Emma Swan. On the wall hung a picture of the two of them on their first date. Emma looked gorgeous in that light pink dress and beautiful blonde hair swinging in her ponytail. 

“I know it was kind of risky decorating it myself and if you don’t like anything we can change-” Emma’s ramblings were cut off once again by her pirates' lips. But this kiss was no peck. A warmness spread throughout her. She could feel a color of rouge flush her cheeks as she skimmed her tongue against the seam of Hook’s lips. he granted her request with gusto while he slipped his hand against her wait. Killian placed a last parting kiss to her lips before pulling back.

“Is this your new way of kindly asking me to shut up?” Emma grinned biting her bottom lip as she twirled a strand of her curly hair.

“Oooh, busted,” Hook chuckled, following her back up the stairs secretly hoping that they could table the dinner and skip right to dessert.

Emma grinned as her pirate pulled out a chair for her, ushering to sit down at the romantic table for two. He was always such a gentleman in every aspect of their dating life. 

The dinner was complete with white linens, candlelight, and his favorite meal, tuna tahini. Which Emma wasn't going to lie, her mother made the food, she still couldn't cook for the life of her, but the thought was there nonetheless. 

They talked for a while about Henry, her family, the latest town crisis and about them. Killian gushed how happy he was to be in her life and to have this second chance at happiness after living for decades in misery. He even brought up that missing year when he and her family were sent back to the Enchanted Forest and Emma and Henry were left clueless in New York.

“I’m really sorry that you had to go through that. It must have been excruciating to have your full memories and know that there was nothing you could do,” Emma apologized reaching for his hand across the soft glow of the candlelight.

“It was most definitely no picnic. That's why I left your family because when I was with them all I could think about was you. So I left hoping it would make things easier but it was no use. No matter what I did I couldn't get Emma Swan out of my head. I even tried to locate that memory potion that your mother took to forget your father but I couldn't track it down, but I’m glad I didn't,” Killian confessed to the gorgeous woman sitting across the table from. 

She batted her eyelashes at him, giving his hand a tight squeeze. “I’m glad you didn't too,” Emma smiled. 

They went back to their dinner and a much lighter topic of conversation. 

“Do you know when your car will be fixed, love? Have they given you a day to pick it up?”

“Why, so we can cross off #5 on your list? Emma smiled as she took a bite of her mash potato. She let the spoon linger between her lips while batting her eyes at the dark haired pirate across the table.

Killian’s eyes stared, pausing putting his fork down. How did she know about his list? He hasn't shown it to her yet and it wasn't even done?

There was a twitch of panic as Killian recalled all the items on that list. He hadn't even planned on showing her some of the things on there!

Emma enjoyed being on the other side of this conversation. There was something about making her man blush that turned her on.

“I might have found it in your drawer while you were in the shower… I was looking for my lotion but I found this instead,” Emma reached into her cleavage pulling out a small piece of paper. The movement exposed a peek of her red lace bra under her dress that she wore especially for tonight. She batted her lashes at Hook as she unfolded it. She could feel the tension in the shared air they breathed. Hook instinctually scratched behind his ear, a nervous tick that Emma had picked up on during their time together.

The list read as followed:  
1\. Sex on a ship  
2\. Ocean sex  
3\. Shower sex  
4\. Sex in the library tower  
5\. Sex in your yellow bug maybe   
6\. Skinny dipping  
7\. 69  
8\. Tantric sex  
9\. Simultaneous orgasms  
10\. Roleplay   
11\. Sex toys  
12\. Sex outside  
13\. Go down on her in her parent's apartment  
14\. Sex in a different realm  
15\. Finger her in a public place  
16\. Watch her touch herself  
17\. Bondage  
18\. Sub dom  
19\. Sex in a stranger's bed  
20\. Spontaneous sex  
21\. Talk dirty in public  
22\. Sexting  
23\. Wench and captain role play  
24\. Anal

“Well, love that list is a rough draft we don't have to do anything on there if it's too much. I know you said make a list but this was just merely brainstorming-” Before he could finish rambling the familiar feeling of Emma’s lips on his interrupted him.

“Killian stop, Do you really think I wouldn't want to do any of these with you? Just thinking about the fact that you were contemplating exactly what you wanted to do to me… Well, let's say that I am more than enthusiastic about this rather adventurous list of activities. In fact, there is one that we both have on our list. Something that no man before has done with me. And I was hoping you’d be up to the task…” Emma beamed tracing her fingers under the arch of his hook, similar to when she teased the metal back in the Enchanted Forest.

Emma watched his face start to understand what Emma was implying. “Emma are you sure? I don’t want to do something you’ll regret,” He pleaded looking lovingly into her eyes.

“Killian, this is on my list too you know,” Emma softly rolled her eyes while moving to interlock her fingers with his across the table.

“I know, love but so was having a threesome and that was something you later regretted. I don’t want you to do something just because I fantasize about it,” He urged taking her palm, giving her a caring stare.

“Killian, I brought you to a boat, well your boat, made you dinner and got all dressed hot as hell fully intending to seduce you with my charm and wit. Do you think this was something I came up with on a whim? And I don't think I could ever regret doing something with you. The reason I regretted it with Neal was because he pressured me into it. You’re not pressuring me at all. This is something I want to do too. At least I think it is?” Emma questioned raising a single brow.

“Emma, you have no idea,” Hook stressed, his Adam's apple bobbing as he tried to swallow.

“Good, you know I’ve been thinking about this since we got stuck in the past,” Emma admitted twirly her hair with her fingers.

“Really, love, what specifically?” Hook asked already feeling his trousers get a bit tighter.

“Well, if I could go back I’d definitely have left that tavern sooner with you,” Emma laughed.

Killian let out a loud chuckle, “I’d hope so. My memory is a little foggy but you definitely did a great job distracting that version of me. What else would you do?”

“Maybe if I could go back, I’d slid my hand up a little further than I did before,” Emma teased, following her own instructions on her Hook in front of her. 

Killian inhaled sharply as he felt her fingers tease the seam of his pants. Slowly creeping her hand up his leg, much further than she did at the tavern all those years ago. 

Emma could see his excitement stirring to life before her eyes. “Then what would you do,” Hook wondered desperately as Emma caressed his muscular high.

“I would have to force myself not to touch the heat growing between my legs until we got back to your ship,” She flirted as she dragged her digits further up, swiping over his manhood.

“Bloody hell, love,” Hook groaned trying to contain the thoughts racing through his mind. At this point, their lips were so close. Their noses nearly touching as Emma continued her ministrations.

“But that’s what I wanted then. Right now I want you to fulfill #24,” Emma smirked, playing with the lace of her bra that was peaking out of her cleavage. 

Before Killian could respond, Emma was straddling him, her lips on his as the ocean breeze nipped at their skin. But all they could feel was the intense heat between their legs. They dueled for control, Hooks hand exploring wildly against the exposed skin of her back. Emma could already begin the feel the heat of her skin rise as he tugged at her bottom lip. She roughly rocked her hips against his, both nearly out of breath already from their passionate frenzy.

I was nearly dark. Only the moon lit the deck as well as a few twinkle lights Emma strung from the sail above. Killian broke the kiss, looking around them at the marina. “Love, what if someone sees?” He wondered, still not able to resist the soft nibbles of his Swan against his neck.

Emma looked around, pausing temporarily. “Looks like we are alone to me. But we can take this below deck if you want?” She flirted, flashing him her green eyes filled to the brim with lust.

Killian didn't need to be told twice. He lifted his lover up, her legs instinctively wrapping around his toned waist. He stepped a few feet to the stairs just barely being able to both fit. Once they were both down to the bedroom their lips were torturing each other again. Hook would never get tired of the feeling of her skin on his. He smiled just thinking of their first kiss. The raw lust, love, and passion that radiated from them was intoxicating. Never again would he have a first kiss like that. And he didn't want to. If he had his way, Emma would be his last first kiss.

He was pulled back to earth when he felt her lips tease the exposed skin of his chest. Hook’s cock was already straining against his zipper. His response time was especially quick tonight even for him. But Emma pulled that out of him. He was like putty in her hands. This had been something that he had been dreaming about since he climbed that bloody beanstalk with her. But he had to be sure once more that this was something she truly wanted, not just to please him.

“Love, are you sure?” He confirmed, pulling back from her embrace temporarily.

“Killian, when a woman begs you to fuck her in the ass don’t argue,” Emma smirked, still pressed up tightly against him, her hand roughly pawing at his backside.

He had never heard her talk quite like that before. And he had to admit that it did things to him. 

Hook attacked her mouth again. This time with less hesitation. He reached behind her with his hook and carefully found the loop of her zipper. Killian slowly unzipped his masterpiece being very careful not to rip her dress. Usually, he would just tear it to shreds but she looked mighty fine in this one particular and wanted to see her in it again. 

It fell to the ground in one smooth motion. Emma stepped out from it leaving her in a red and black corset and a matching lace thong.

“Happy Birthday,” Emma grinned. Her breasts were perfectly contoured and the corset hugged all the right places. Her waist accentuated and her breasts seemingly defying gravity, and her ass exquisitely shaped peeking from her thong. She looked good enough to eat.

Emma knew her little outfit would rend her pirate speechless, which doesn't happen very often. “Well, are you just gonna stand there or are you gonna take me, Captain?” She commanded with her arms on her hips.

“Don’t start what you can’t finish, princess,” He warned flashing her a seductive grin.

“Oh, I think I can handle it,” Emma winked.

With that last sentence, Killian was back kissing her. He let his hand freely roam her body, testing his own limits. He was already painfully hard and he had barely even touched her yet. He knew he was in for a long night. 

Emma felt another rush of moisture between her legs as Hook spun her around pressing his clothed length against the crease of her ass almost teasing her for what has yet to come. Hook playfully bite the crook of her neck skirting the line of pain and pleasure. He continued to kiss down her shoulder, then trailing to her back. Placing a kiss down each vertebra until he could feel her whole body shudder and goosebumps spread across her skin. 

Emma leaned her head back against his chest, giving him as much access as she could begging for more. As he suckled the soft lobe of her ear he let his hand and hook venture the sides of her thighs and up to her swollen breasts. He could feel her nipples tighten against his touch even through the lace. Emma let out a hiss when she felt her pirate pinch one into a sharp point. Emma heard a slight shuffling behind her as she caught his dress shirt and vest fall to the floor out of the corner of her eye.

Killian groaned when he felt his savior tease his center with her backside, torturing him further. “Impatient are we, love?” He whispered into her ear. Emma simply moaned in response, too turned on for words.

“Are you wet for me, Emma? I bet you are. Should I find out?” Hook challenged the goddess before him. He found her lace covered sex already feeling her sweet nectar soaked through her panties.

Emma couldn't stand it anymore. She needed to be closer to him. Spinning around, she found his lips once again claiming it as hers. Hook worked as fast as he could to discard her bodice. He loved the way she looked in it, but he needed to see her completely bare. After a few impatient moments, Emma instructed him to rip the laces off the back which he happily obliged leaving her nearly nude. All that was left was her thong and black stiletto pumps which she looked breathtaking in.

Emma pulled back, pausing from their makeout session for a second. Hook confusingly watched her walk over to his nightstand and pull out an array of clear liquids which he had recently learned the name of. He always thought that “lube” was such a silly name for such a serious activity.

“Told you this wasn't a spur the moment decision for me,” Emma smiled flashing him a signature Hook look lifting her brow.

It did bring him some reassurance that Emma did not decide this lightly. She really did want this just as much as he did. 

Killian strode over to his Swan, cupping his hand over her cheek, “Know that you can change your mind at any time, love, okay? Promise you’ll tell me if you ever want me to stop,” Hook urged.

“Promise,” Emma assured him.

Her body radiated from excitement and maybe a little from nerves. He instructed her to lay down on her stomach on the bed. She heard him shuffle over to the nightstand reaching for one of the bottles. 

She closed her eyes, trying to focus on her breathing when she felt her pirate's warm rough hands against her skin. The oil let his palms slid with ease across her muscles as the sweet aroma filled the air. Emma sighed deeply as Killian’s fingers worked slowly again her skin. He took his time easing the tension from each inch of her body. Emma thought they were going to get right to the main course but she was sorely mistaken. 

“This particular activity can be quite enjoyable for both parties, but it is superlative that you’re relaxed. So, love I want you to close your eyes and just feel. And when something feels good tell me,” Killian requested as he worked out several knots in her shoulders.

Every once and a while he could hear her moan which was music to his ears. There was nothing more beautiful than to hear his Swan mewl for him. He admired the softness of her skin as he wiped away the worries from her body. He knew that as a Mother, daughter, sheriff and savior that her life had its challenges. He did everything in his power to convince her to take some time for herself but Emma was selfless. Which was one of the many things he loved about her but he knew even saviors need breaks. He was glad that he could make her feel good, even if it's just for a moment. But tonight, her pleasure was going to last a little longer than a few minutes. Tonight was reserved for them.

Emma felt the cool steel of his hook slid down the center of her back leaving goosebumps in its wake. She secretly loved it when he used his namesake on her. But truthfully she didn't hide that secret of hers well. She knew it turned him on when she asked him to use it on her.

Emma purred as she felt his hand drift a little lower down her spine. He worked his fingers a bit deeper allowing Emma to moan in response. Killian followed his current trajectory and teased the swell of her ass. Her body still covered in the sweet smelling oil as Hook kneaded the flesh in his hand. He skimmed his fingers against the lace of her panties, spreading the oil under the lace. She remembered the first time she introduced her pirate to a thong. She thought he was going to have a stroke the first time she wore one. She never would forget his face when he undressed her like any other night only for him to find a tiny scrap of satin covering her sex. 

Once Killian was satisfied with his work he moved down to her legs. They were one of his favorite parts of his Emma. They were so long and luscious, her skin so milky white. He could get lost between them for days. Hook worked his way down the back of her thigh, pausing slightly at the inside of her knee. He leaned down to kiss the skin, letting his beard tease the sensitive flesh before making his way down to her toes. 

He picked up her right leg, bending it at the knee to meet his lips. He kissed down her ankle before discarding her heels, stopping briefly to tease the arc of her foot. He then continued to give her the best foot massage of her life. She wondered how a man with one good hand could possibly give her more pleasure than a man with two. She asked that question a lot, but it usually did not concern foot massages. 

Killian followed suit with her other leg, leaving no inch of skin untouched before finding his way back to her neck. Emma’s fingers grasped the quilt under her as she felt him suck at her pulse point. The motion causing her to close her eyes, wondering what was next to come. 

After a moment she felt the absence of his touch. She missed it, craved it in fact. Emma almost stuck her head up to look for him until she felt his hand and hook pry her legs open. 

She thought that maybe this meant they were going to get on to the main course now? Her heart started to beat faster as the anticipation drove her mad. She felt a slight tug at her hip partnered with a dull rip. She soon figured that it was her thong which was shred to pieces on the floor. Emma was used to it. If she had a dollar for every pair of underwear he had ruined she could buy the Storybrooke Mansion. 

Killian admired how visibly wet she was already. The insides of her thighs were coated in her excitement, just begging him to take her right then and there. But Hook wanted her good and ready before he had his way with her. He could see Emma was just as impatient maybe even more than he was already. She kept trying to not so subtly raise her ass in the air, tempting him to claim her but Killian exercised his restraint. 

“Be patient, love. But I do love your enthusiasm,” He grinned as Emma pouted flashing him a cute yet displeasing look.

Killian leaned down between her splayed thighs. Emma could feel his breath against her folds. The feeling alone had her on the edge before he even touched her. She shuddered when she felt his fingers part her open for him. Before she could brace herself his tongue was buried between her legs. Her flesh nearly hot to the touch as he drank in her sweet essence. Hook had to work to keep her from bucking her ass up into his face as she greedily wanted more. 

Killian could hear her muffled cries as she buried her face in the blanket under her. He worked his mouth over her folds as he did his best to relieve some of the tension between his own legs against the bed. 

“Killian I’m so close,” He heard faintly escaping his Swans lips. He took her sensitive bud between his lips, sucking hard until she saw stars. He lapped up her release, loving the taste of her on his tongue. 

Emma was still trying to catch her breath when she felt him spread her cheeks and delve between her cheeks. She’d never felt anything like it. Every nerve was on fire. Nerves that she didn't even know existed but she was thankful she knew now. She whimpered in pleasure as she felt Killian tease his tongue around her puckered hole. The sensation was not what she expected at all. She had no idea that it would feel this good.

Killian thought he'd heard her mumble something under her breath. Which turned out to be “more” which had been a very common word tonight so far. He heeded her request returning back to his previous ministrations. Every time he heard her cry out in pleasure his cock got a little harder in his trousers but he wanted to focus all his attention on her. He vowed to make this a good first experience for her knowing just how fun it can be for the both of them when done right. The most important thing during this activity especially was communication and he hasn't heard much from his Swan beside moans of pleasure which he wasn't complaining, but he needed to make sure she was still on board so to speak.

“You haven't changed your mind right, love?” Hook wondered from behind her.

Emma pushed her backside up giving him full access to any and everything he desired. “No, have you?” She smiled, batting her long dark lashes at him. 

“Hell no, love,” Killian assured her, still kneading her skin.

“So, Captain, what's next?” Emma grinned knowing how much he loves it when she called him that.

“Next, I’m going to open you up. I want to make sure you’re ready. I’m going to do my best to make sure that this is as painless as possible, love. But I can’t promise that there won’t be some discomfort at first, okay?” He vowed sincerely.

“I trust you,” She promised him as she bucked her ass against him showing her just how much she wanted this. Emma did trust him. She trusted him more than anyone before, especially any man. But she still couldn't help to be nervous. She did her best to hide it but she knew her pirate could read her like an open book.

She felt Killian pour more of the sweet smelling liquid between her cheeks. It slid past her tight hole and down to her pussy, the lube mixing with her already wet sex. Emma closed her eyes as Hook slid his digits with much ease through the crease of her ass. He watched as her muscles tightened as his fingers passed over the ridged ring. He circled his thumb around the hole, easing her to relax.

“Just breathe, love, deep breaths,” He encouraged her softly as he continued his ministrations.

Emma heeded his advice, beginning to take nice long breaths. She inhaled smelling the sea air and strawberry lube as she began to unwind. Hook felt her body soften against him hoping that it was a sign that she was calm enough for the next step.

Killian slowly and carefully pressed his slick digit into her puckered hole. He sang her words of encouragement and endearment the whole way. “That’s it, love. Just like that,” He mewled, her walls tightly enveloping his finger. God he knew she would feel so spectacular around his cock, she always did. But he knew that tonight was going to be a little different. Nothing would ever replace the drag of her tight welcoming quim pulling him over the edge but he had a feeling that tonight would be a close second.

Hook slid against her slowly, listening intently to her every breath. He felt her muscles contract against his digit as he gradually picked up the pace. He soon felt Emma relax, even meeting him halfway pushing herself faster and harder against him. Killian took this as a sign and added another finger to the mix twisting them playfully, testing just how far he could stretch her. 

“You love this don’t you, Emma. You can’t wait for my cock to fill you up can’t you?” Hook growled as he pumped in and out of his wanton princess before him. Emma lifted her head up, turning to face him. Their eyes met blue chasing green as a sexy grin formed upon his Swan’s face.

“Bloody hell, I’d kill for another hand right about now,” Killian groaned feeling his cock pull against his trousers.

“I’d say you’re doing just fine with one,” Emma crooned driving herself back against him. Hook grinned like the Cheshire cat at his Swans last comment. She knew how self-conscious he was about his disability. Killian would never forget the first time he had confided in her about his insecurities. She simply raised his hook to her lips kissing it, showing just how much she cared for him just the way he was. It meant everything to him. Nearly every women before her had been repulsed by it or only looked at it as some sort of fetish, which he didn't quite mind the latter but it was so important to him that he wasn't looked at as less. Emma never treated him as such.

Emma could feel her folds getting wetter and wetter by the second. She had no idea how much this whole ordeal would turn her on. She tried to press her legs together, attempting to create some sort of pressure to relive the fire igniting within her. But all she could do was hold on to the sheets beneath her and hold on for the ride.

She heard rustling behind her. The sounds of a zipper opening and her whipping her head toward the sound, desperate yet hesitant for what has yet to come. But she made a promise to herself to fully trust the pirate before her (or well behind her). Emma did not easily give herself over to another person let alone trust someone completely with her whole heart and body. But that changed the moment she met Killian. She definitely wanted this. That was very evident between her legs and by the looks of her pirate he wanted this too. 

Without warning, Emma felt the loss of his fingers inside her. She sharply exhaled when she heard a rip. Emma watched impatiently as Hook rolled a condom down his engorged length. 

“Are you sure, love?” Killian lovingly asked one last time.

“Yes,” Emma simply replied.

“Promise, darling? Remember we can stop any time,”

“I promise, Killian. I trust you,”

Emma watched as her pirate slid his cock through her sodden flesh basking in her arousal. Hook reached for the bottle he previously used, reapplying copious amounts of lube to his member and through the crease of her ass.

Emma felt his hand sneak over her hip swiping a clean finger over her sensitive clit. Instantly feeling the start of her orgasm building deep inside. With her release not far behind he began to slowly push himself at her opening. Emma could feel her body try to resist the intrusion but the sensation of his digit swirling over her over stimulated flesh distracted her just enough to make the pressure bearable. In fact, it wasn't nearly as bad as she thought it would be. 

Emma focused all her effort on her breathing as she felt more and more of his length slid inch by inch inside of her. She could tell the speed of the intrusion was killing Hook. She knew it took all the strength he had not to take her fast and hard but Emma appreciated the tenderness of his actions. 

Emma started to feel a dull aching pressure start to spread throughout her, fisting the sheets under her fingers. She knew Hook had sensed her discomfort as he paused his movements which she knew must have been painful for him.

“Do you want me to stop, love?” Emma hearing the hints of worry and care in his voice. She looked back shaking her head confidently. 

“Touch yourself, love,” Hook urged his princess. Emma’s hand heeded his command flying to her clit. A rush of moisture shot straight to her sex as she circled the sensitive bud. She felt her pirate resume his ministrations, pushing himself further and further. The pressure faded into pleasure in seconds as Killian enjoyed the feeling of being fully seeded in his Swan. 

 

Hearing her moans just made him want her more and Emma knew it. The next time he thrust into her she gave him an extra squeeze testing his stamina and willpower. She looked utterly debauched, her hair a mess and her eyes dark with lust. He listened carefully noting which movements elicited the most pleasure. It was almost as if Emma was making music as they made love with sweet sounds of highs and lows depending on their movements. Sharper thrusts tended to make her moan higher while more languid ones made her purr, catlike and sultry. 

She moaned between thrusts, the slick sound of skin against skin turning her on even more which Killian thoroughly enjoyed. Emma wasn't usually vocal like this during sex which made the whole ordeal even sweeter. 

“You like this don’t you my wanton princess?” Hook growled punctuating his question with a hard thrust. Emma merely nodded, so overwhelmed that she could barely string a single sentence together.

Hook brought his hand to her right cheek playfully giving her a swat watching the flesh turn from pale to pink “No, love I want to hear you say it. I want you to tell me how much you love it,” It was with that last sentence that Emma knew she had awoken the pirate which was far from a bad thing. In her opinion, he came to visit all too rarely so she wasn't about to take it for granted. 

He brought down his hand again, this time even harder enjoying the mirror image of his hand form on her skin. “I love it! Please, don’t stop!” Emma begged as his thrusts increased.

“Fuck yourself, Emma. I want to feel your fingers against my cock,” He ordered.

Emma heeded his request sliding her digit into her slick sex shuttering as she felt him fuck her on the other side of her walls. That feeling alone had her teetering on the edge loving the sensation of his pulsating inside her.

The chords of his neck strained as he felt his impending orgasm start to form at the bottom of his spine. But Emma beat him to it. Her orgasm wrecks her, barreling through her body in rippling waves. 

The pull of her walls dragged him toppling over the edge with her. He slowed the drive of his hips until he was spent.

“That was a one time thing,” Emma exhaled slumping into the mattress. Killian frantically searched for her eyes fearing the worst. Did she not enjoy it? Did he do something wrong? Then he caught the smirk upon her face. “Oh my god I’m sorry I was kidding!” Emma laughed cuddling up to him.

“Bloody hell, love you can’t do that to a man!” Hook sighed in relief. “You don’t understand Emma I still have nightmares about that phrase,” He jested rubbing her back.

“I’m sorry, but you should have enough faith in us to know that nothing in our relationship was a one time thing” Emma pouted places a chaste kiss to his lips.

“So…I can expect this every year for my birthday?” Killian wondered ever so adorably. 

“Maybe if you’re good…” Emma flashed him a flirty grin while running her hands up and down his chest.

“My god you are the perfect woman Emma Swan,” He professed while lovingly brushing a stray hair behind her ear. Emma smiled back at him basking in the afterglow of their passionate lovemaking. 

After a few moments, Emma picked up Hook’s folded list of desires and studied it. “Why do most of these require me to get wet?” Emma asked instantly regretting the phrasing of her question.

“Well, love the all do if you’re doing them right,” Hook winked playfully.

“So my list or your list next time around?” Emma wondered running her hands through his chest hair.

“As always it’s the ladies choice,” Killian winked sliding his hand down her back.

“Mmm, what should I torture you with next?”

**Notes for the Chapter:**

> Thank you for reading! As always leave a like, comment, prompt or suggestion! What should Emma and Killian do next? Follow me on tumblr @captain-swan-coffee!

**Author's Note:**

> Thanks for reading! If I write a part two what should they cross off next? ;) As always leave a like, comment, prompt, suggestion etc! Follow me on tumblr @rubyrose82 or my Captain Swan blog @captain-swan-coffee


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